Carbon Dioxide-Catalyzed Stereoselective Cyanation Reaction

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Title
Carbon Dioxide-Catalyzed Stereoselective Cyanation Reaction
Author(s)
Tamal Roy; Myungjo J. Kim; Yang Yang; Suyeon Kim; Gyumin Kang; Xinyi Ren; Anders Kadziola; Hee-Yoon Lee; Mu-Hyun Baik; Ji-Woong Lee
Publication Date
2019-07
Journal
ACS CATALYSIS, v.9, no.7, pp.6006 - 6011
Publisher
AMER CHEMICAL SOC
Abstract
© 2019 American Chemical Society.We report a Michael-type cyanation reaction of coumarins by using CO2 as a catalyst. The delivery of the nucleophilic cyanide was realized by catalytic amounts of CO2, which forms cyanoformate and bicarbonate in the presence of water. Under ambient conditions, CO2-catalyzed reactions afforded high chemo- A nd diastereoselectivity of β-nitrile carbonyls, whereas only low reactivities were observed under argon or N2. Computational and experimental data suggest the catalytic role of CO2, which functions as a Lewis acid, and a protecting group to mask the reactivity of the product, suppressing byproducts and polymerization. The utility of this convenient method was demonstrated by preparing biologically relevant heterocyclic compounds with ease
URI
https://pr.ibs.re.kr/handle/8788114/6063
ISSN
2155-5435
Appears in Collections:
Center for Catalytic Hydrocarbon Functionalizations(분자활성 촉매반응 연구단) > Journal Papers (저널논문)
Files in This Item:
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